Structural revision and total synthesis of caraphenol B and C

Org Lett. 2011 Oct 21;13(20):5524-7. doi: 10.1021/ol2022406. Epub 2011 Sep 26.

Abstract

Chemical syntheses of two stereochemically unique resveratrol dimers, caraphenols B and C, have shown that their structures are misassigned. Thoughts on their potential chemical etiology led to an alternate structural proposal that has been confirmed through synthesis, one indicating that the substituents on their respective indane systems exist in a relative trans,trans orientation rather than the originally postulated all-cis arrangement.

Publication types

  • Research Support, N.I.H., Extramural
  • Research Support, Non-U.S. Gov't
  • Research Support, U.S. Gov't, Non-P.H.S.

MeSH terms

  • Crystallography, X-Ray
  • Molecular Structure
  • Phenols / chemical synthesis*
  • Phenols / chemistry
  • Resveratrol
  • Stereoisomerism
  • Stilbenes / chemical synthesis*
  • Stilbenes / chemistry*

Substances

  • Phenols
  • Stilbenes
  • caraphenol B
  • caraphenol C
  • Resveratrol